How to Create a Culture of Ongoing Sales Development
- LMSPortals
- 10 minutes ago
- 7 min read
Many companies still look at sales training as a one-off event. They onboard new hires, hand them a playbook, maybe run a two-day workshop—and that’s it. After that, they expect reps to fend for themselves, chase targets, and magically keep improving.
But in today’s markets, that approach is outdated and costly. Buyer expectations keep changing. New competitors pop up with fresh tactics. Technology reshapes the way prospects research and buy. If your sales team is only learning once in a while, they’re not just standing still—they’re falling behind.
Creating a culture of ongoing sales development is how you future-proof your team. It means salespeople aren’t just executing today’s strategy—they’re constantly getting sharper, adapting to shifts, and actively raising the bar.
So how do you build such a culture? Let’s break it down.
Why You Can’t Afford to Skip Ongoing Development
Sales Is a Moving Target
Sales isn’t a static profession. Prospects have more information than ever before. They’re 60-70% of the way through their buying journey before they even talk to your team. Your reps have to bring insights that go beyond what the prospect can Google.
Meanwhile, new sales methodologies (like MEDDIC, Challenger, or Gap Selling) and tools (like AI-driven CRM insights or video prospecting platforms) are always emerging. If your team isn’t staying up-to-date, they’ll get outflanked.
It Keeps Your Best People
Top performers don’t want to stagnate. They want to grow their skills, take on bigger challenges, and see a clear career path. If they don’t, they’ll start returning recruiter calls. Companies with strong development cultures enjoy higher retention because employees feel invested in and see a future with the company.
It Directly Improves Results
This isn’t theory. According to research by CSO Insights, companies with a structured and continuous sales development program saw their quota attainment improve by more than 15%. Deal cycles shorten, win rates go up, and average deal sizes often grow—because reps are consistently refining how they sell.
The Core Principles of an Ongoing Development Culture
1. Learning Isn’t “Extra”—It’s Expected
If training is treated like an interruption from “real work,” reps won’t engage. In a strong sales culture, development is baked into the job. Just like hitting pipeline targets or submitting forecasts, improving skills is part of what’s expected.
This mindset starts with how managers talk about growth. If they position it as a distraction or a “nice-to-have,” reps will too.
2. It’s a Two-Way Street: Managers and Reps Grow Together
Often companies pour effort into rep training but ignore frontline managers. Yet these managers shape day-to-day culture. They set expectations, run pipeline reviews, and do (or skip) coaching. If they’re not developing themselves—learning how to be better coaches, better motivators—the whole system stalls.
Strong cultures of development see managers actively participating, not just enforcing.
3. It’s Measurable and Celebrated
People pay attention to what gets measured. If you only celebrate closed deals, that’s where reps will focus. But if you also track progress on skills—through certifications, observed improvements in calls, or peer feedback—you send a clear signal: mastery matters.
Publicly recognize growth milestones. When someone finally nails value-based discovery questions after struggling, highlight it in team meetings. It builds momentum.
How to Build This Culture, Step by Step
Lead from the Top
Executives and senior leaders set the tone. If the CRO never mentions skill building, or the CEO only talks about quarterly revenue, managers will prioritize short-term targets over development.
Have your leadership team share what they’re learning. For example, “This quarter I’m working on improving how I give tough feedback.”
In all-hands or sales kickoffs, include sessions on skill growth, not just number reviews.
Encourage execs to join or even facilitate some trainings—it sends a powerful message.
Hire People Who Love to Learn
You can’t build a culture of growth with people who don’t want to grow. So adjust your hiring process:
Ask questions like:
“Tell me about the last thing you taught yourself that wasn’t required.”
“What’s the best piece of constructive feedback you’ve ever received?”
“What’s a skill outside of work you’ve spent time improving recently?”
Look for signs of curiosity and humility. If candidates get defensive talking about mistakes, they’ll resist coaching later.
Build a System of Continuous Learning
Onboarding is crucial, but it’s just the start. Your real power is in what comes after.
Some ideas:
Weekly micro-trainings: 15-20 minute sessions that tackle one specific topic—like overcoming budget objections or using new CRM features. Keeps learning constant without overwhelming reps.
Monthly skill workshops: Longer sessions for hands-on practice, like running mock discovery calls or building account plans.
Quarterly certifications: Formal milestones that deepen expertise, such as mastering a multi-step negotiation process or completing a MEDDPICC evaluation.
Annual sales kickoffs: Reinforce and re-energize the culture with guest speakers, new frameworks, and team challenges.
Keep sessions tied to real deals and issues your team faces. Theory alone doesn’t stick—application does.
Make Peer Learning a Pillar
Some of the best insights come from your own top performers. Build systems where they naturally share:
“Lunch & Learn” sessions: Have a rep who crushed a big upsell run a casual session explaining how they structured it.
Deal dissections: Regular team reviews of wins and losses. Everyone learns from what worked—or what didn’t.
Shadowing and call libraries: Pair new reps with seasoned sellers, or build a library of recorded calls highlighting strong techniques.
This not only spreads best practices but also strengthens team bonds.
Prioritize Coaching (and Do It Right)
A coaching culture is one of the strongest predictors of sales success. But real coaching isn’t just “How’s your pipeline?” It’s:
Reviewing calls together and breaking down what went well or what could improve.
Practicing new techniques in low-stakes role plays.
Setting small improvement goals (“This week, focus on asking two more follow-up questions before pitching.”) and tracking them.
Make it non-negotiable:
Block time each week for coaching on calendars.
Hold managers accountable for the quality and frequency of their coaching, not just their team’s numbers.
Leverage Technology to Scale It
Modern tools can supercharge ongoing learning.
Conversation intelligence platforms (like Gong, Chorus): Automatically record and analyze calls, making it easy to coach on real examples.
Microlearning apps: Deliver bite-sized lessons reps can complete between calls.
CRM-linked dashboards: Show both performance metrics and progress on skills training, so development stays front and center.
Even something simple like a Slack channel where people share tips, articles, or celebrate small wins can build energy around learning.
Keeping the Culture Alive: Sustain and Evolve It
Tie Learning Directly to Career Progression
Reps are more motivated when they see a payoff. Make clear how mastering certain skills or hitting development milestones opens doors—whether it’s eligibility for major accounts, promotions to team lead, or moving into strategic sales.
This shifts learning from “something management wants” to “something I want to accelerate my career.”
Recognize and Reward Progress
Recognition is fuel. Don’t just wait for closed deals to give shoutouts. Highlight reps who:
Completed a tough new certification
Showed big improvement in discovery calls
Took the lead running a training session for peers
Pair praise with tangible perks—like bonus comp, public recognition in company-wide meetings, or first pick of leads.
Keep Listening and Iterating
The best development cultures evolve. What worked for your team two years ago might not work today.
Run quick pulse surveys after training cycles.
In one-on-ones, ask: “What training or coaching would help you most right now?”
Review your programs at least twice a year to add new topics, sunset stale ones, and stay aligned to market shifts.
Common Pitfalls to Avoid
Trying to Do Too Much at Once
Flooding your team with a dozen initiatives at once usually backfires. They’ll see it as noise. Start with a few high-impact habits—like weekly coaching sessions and monthly skill workshops—and build from there.
Making It Feel Like Compliance
If learning is just another box to tick (“complete these three modules to be compliant”), people disengage. Keep it tied to real-world deals. Have them bring in active opportunities to role-play or dissect in sessions.
Forgetting to Train Your Managers
This is huge. Frontline managers often rise from top rep roles without much leadership training. They need help learning how to coach, run impactful one-on-ones, and give feedback. If they aren’t good at it, your culture stalls.
The Payoff: A Team That Doesn’t Just Meet Quota—It Redefines It
When you truly embed ongoing sales development, your team changes in powerful ways:
Reps self-correct. They look for ways to improve, ask for feedback, and adapt without needing to be pushed.
Managers evolve. They spend more time developing people, not just inspecting forecasts.
Your entire org becomes more agile. When markets shift, you’re not scrambling to catch up—your team already has the habit of learning and adjusting.
The ROI is clear: higher win rates, bigger deals, faster ramp times for new hires, and a salesforce that sticks around because they’re growing.
Summary
Creating a culture of ongoing sales development isn’t about adding more trainings to your calendar. It’s about making learning part of your team’s DNA—something that happens every week, in every coaching session, every peer conversation, every pipeline review.
It starts with leaders setting the example and continues with systems that support, measure, and celebrate growth. Over time, it transforms your team from order-takers into trusted advisors and from quota chasers into consistent market leaders.
Ready to start? Pick one area—like instituting a weekly skills huddle or having managers block real coaching time—and build from there. In six months, you’ll be amazed at how far your team has come.
About LMS Portals
At LMS Portals, we provide our clients and partners with a mobile-responsive, SaaS-based, multi-tenant learning management system that allows you to launch a dedicated training environment (a portal) for each of your unique audiences.
The system includes built-in, SCORM-compliant rapid course development software that provides a drag and drop engine to enable most anyone to build engaging courses quickly and easily.
We also offer a complete library of ready-made courses, covering most every aspect of corporate training and employee development.
If you choose to, you can create Learning Paths to deliver courses in a logical progression and add structure to your training program. The system also supports Virtual Instructor-Led Training (VILT) and provides tools for social learning.
Together, these features make LMS Portals the ideal SaaS-based eLearning platform for our clients and our Reseller partners.
Contact us today to get started or visit our Partner Program pages